U.S. Pat. No. 5,024,742, issued Jun. 18, 1991, to Nesburn et al., discloses a method of crosslinking amino acid-containing polymers with photoactivatable, heterobifunctional crosslinking agents, the crosslinking agents having a photoactivatable site and a conventional site, comprising: i) selecting one or more amino acid-containing polymers; and ii) combining the polymers with the crosslinking agents such that the conventional site on the crosslinking agent is bound to the polymer and the photoactivatable site is unbound. Upon photoactivation, crosslinks are formed when the photoactive site binds to another amino acid-containing polymer. The resulting crosslinked collagen composition can be used as a bioadhesive for sutureles closures of the eye or any other wound.
U.S. Pat. No. 5,156,613, issued Oct.20, 1992, to Sawyer, discloses a method of joining or reconstructing biological tissue comprising applying energy to the tissue while providing a filler material to is and denaturing or melting the material and adjacent biological tissue with the energy to cause mixing of the denatured or melted filler material and tissue, thus joining or reconstructing the tissue. Also claimed is a method of joining or reconstructing biological tissue comprising applying optical or radio frequency energy while providing a collagen filler material to the biological tissue; denaturing or melting the collagen and adjacent tissue with the applied energy to cause mixing of the denatured or melted collagen and tissue; and joining or reconstructing the tissue.
U.S. Pat. No. 5,162,430, issued Nov. 10, 1992, to Rhee et al., and commonly owned by the assignee of the present invention, discloses collagen - synthetic polymer conjugates prepared by covalently binding collagen to synthetic hydrophilic polymers such as various derivatives of polyethylene glycol.
U.S. Pat. No. 5,192,316, issued Mar. 9, 1993, to Ting, discloses a lens for implantation directly on the Bowman's membrane of a live cornea to correct the optical properties of the eye. The lens is made of a synthetic polymer which is permeable to water and forms a hydrogel. The lens preferably includes an additive to increase the adhesion of the lens to the cornea and/or to stimulate the growth of epithelial cells. The additive may be fibronectin, collagen, cell fastening protein, antigelatin factor, a biologically active peptide, cold insoluble globulin, chondronectin, lanlinin, epithelial growth factor (EGF), or a mixture thereof.
U.S. Pat. No. 5,209,776, issued May 11, 1993, to Bass et al., discloses a composition for bonding separated tissues together or for coating tissues or prosthetic materials comprising: i) at least one first component selected from natural or synthetic peptides, modified, crosslinked, cleaved, or shortened variants or derivatives, and ii) at least one second component, which is different from the first component, adapted to support the first component to form a matrix, sol, or gel with the first component. The first component may be, for example, albumin, alpha-globulins, beta-globulins, gamma-globulins, transthyretin, fibrinogen, thrombin, collagen, elastin, keratin, fibroin, fibrin, or fibronectin. The second component may be, for example, hyaluronic acid, chondroitin sulfate, dennatan sulfate, keratan sulfate, heparin, heparan sulfate, collagen, fructose, dextrans, agarose, alginic acid, pectins, methylcellulose, hydroxycellulose, hydroxypropylmethylcelulose, hydroxyethylecellulose, CMC, glycerin, mannitol, sorbitol, polyvinylalcohol, or polyethylene glycol.
U.S. Pat. No. 5,219,895, issued Jun. 15, 1993, to DeVore et al., discloses a collagen composition, useful as an adhesive for medical applications, wherein the composition is formed by the polymerization of derivatized collagen, modified with an acylating agent and/or a sulfonating agent. The polymerization is performed by explosive UV irradiation, fluorescent light, and/or an initiator. The acylating agent may be glutaric arthydride, succinic anhydride, lauric anhydride, diglycolic anhydride, methyl succinic arthydride, methyl glutaric arthydride, dimethyl glutaric anhydride, or exo-3,6epoxy-1,2,3,4-tetrahydrophthalic arthydride. Bonding of soft tissue comprises applying a polymerizable collagen composition onto at least a portion of a surface of at least one of a first and second tissue; exposing the tissue surface to an initiator to polymerize the collagen; and contacting the two tissues to form a bond between them.
U.S. Pat. No. 5,290,552, issued Mar. 1, 1994, to Brown et al., discloses a surgical adhesive composition comprising fibrinogen, actor XIII, collagen, thrombin, and Ca.sup.2+ ions in an aqueous medium. The collagen is fibrillar, is insoluble at pH values about 5, is flowable, has the native helical structure of collagen fibrils, and is capable of causing gelation of the adhesive. The thrombin and Ca.sup.2+ are present in an amount sufficient to catalyze polymerization of the fibrinogen to form a clot.
Commonly owned U.S. Pat. No. 5,328,955, issued Jul. 12, 1994, to Rhee et al., discloses various activated forms of polyethylene glycol and various linkages which can be used to produce collagen--synthetic polymer conjugates having a range of physical and chemical properties.
European patent publication No. 341007, to Matrix Pharmaceuticals, Inc., discloses a surgical adhesive composition comprising, in an aqueous composition, plasma from the patient to be treated, collagen in an amount sufficient to thicken the composition (e.g., at a concentration of about 5-30 mg/ml), and thrombin in an amount sufficient to catalyze polymerization of fibrinogen present in the plasma to produce a clot (e.g., about 1-1000 N1Hu thrombin).
European patent publication No. 466383, to Bausch & Lomb Inc., discloses an adhesive composition suitable for surgical applications comprising an aqueous solution of natural collagen which has a melt index temperature of 35.degree.-45.degree. C. The composition comprises a blend of densely crosslinked collagen and non-crosslinked collagen. The densely crosslinked collagen is achieved by thermal crosslinking. PCT publication No. WO 9213578, to Bausch & Lomb Inc., discloses a surgical adhesive composition comprising an aqueous collagen or gelatin solution with a melt index temperature (MIT) of 33.degree.-60.degree. C. Healing of wounds is promoted by contacting at least one surface of the wound with a composition comprising: a) a dispersion of cultured epithelial cells in an aqueous collagen solution, or b) an aqueous solution containing a purified naturally occuring biopolymer and growth factors, wherein the composition has an MIT of 33.degree.-60.degree. C. and a viscosity of less than 50,000 cP at 10.degree. C. above the MIT.
European patent publication No. 575273, to Flamel Technologies, discloses crosslinkable collagen derivatives that are soluble in water and/or polar aprotic organic solvents and contain free or substituted --SH groups on cysteine or cysteine derivative residues attached to the collagen molecule, at least in part, through spacer groups. Also disclosed is insoluble crosslinked collagen in which the interchain bridges are, at least in part, disulfide linkages formed by cysteine residues attached to the collagen molecule, at least in part, through spacer groups. The claimed compositions are useful as biological or surgical adhesives.
Japanese patent publication No. 6070972, to Nippon, discloses a composition for adhering biological tissues consisting of i) an adhesive ingredient comprising a partial hydrolysate of collagen protein, water, and a polyhydric phenol compound; and ii) a hardening ingredient consisting of an aqueous solution containing at least one of formaldehyde, glutaraldehyde, and glycerol aldehyde.
Commonly owned, allowed U.S. application Ser. No. 08/147,227, filed Nov. 3, 1993, by Rhee et al., discloses collagen-polymer conjugates comprising chemically modified collagens, which are in substantially nonfibrillar form at pH 7, covalently bound to synthetic hydrophilic polymers to produce optically clear materials for use in ophthalmic or other medical applications.
Each publication cited above and herein is incorporated herein by reference in its entirety to describe and disclose the subject matter for which it is cited.
We now disclose a detailed description of preferred embodiments of the present invention, including bioadhesive compositions comprising collagen crosslinked using multifunctionally activated synthetic hydrophilic polymers, and methods for using these compositions to effect adhesion between a first surface and a second surface, wherein at least one of the first and second surfaces is a native tissue surface.